Jimmy Osmond: "Losing all our money was the best thing to ever happen to us"

At 16 I was still figuring out what I wanted to be when I grew up. I never thought showbiz would last for me. I’d already had some hit records – my first when I was five. Long haired Lover from Liverpool came out when I was eight. By the time I was 16 I had my own advertising agency, which sounds bizarre, but my family had a TV studio and I wanted to do my own thing. So I was running that, working with a lot of crazy clients like Yamaha and Coca-Cola. And I was in the TV show Fame. But I was still figuring out what I wanted to do. I loved music so I was still recording but no one really wanted to hear from me – I was kinda like Bob the Builder, this child star. I had the notoriety but no one cared. That was hard.

I was into pretty girls and fast cars. It was hard, really getting to know a girl. I dated a lot of girls around the world but I was quite shy and insecure, like most entertainers. So I never really pushed the romance thing until I knew I’d found my soul mate.

I first met my wife when she was babysitting for my brothers’ kids. I thought she was stuck-up and she thought I was too groovy because I wore leather pants and drove a De Lorean. Then later we ran into each other at our church and I ended up taking her to a movie. She was different to other girls I dated. She knew who she was, and she wasn’t into the whole showbiz thing. She knew who we were obviously but she was more into classic rock. But so was I! We’ve been married 25 years and we have four kids.

Jimmy with his brothers in The Osmonds.

I always loved showbusiness because it was all I knew. And I love what it does, makes people forget their troubles for a few hours – that’s a cool business to be involved in. Sometimes being in the public eye gets tiring but you know what? It’s so easy to get out of showbusiness. [Regarding Justin Bieber’s comments that he won’t pose for any photos with fans]. If Justin Bieber wanted to get out he could. I have no patience or time for anybody who doesn’t have time for the people who made it happen for them. That is just the most selfish, self-absorbed comment that anybody could ever make. I understand where he’s coming from but I don’t respect it. People would kill for the opportunities he’s had, to even have their records heard.

When I look back at the 16-year-old me, I see that he was very independent but a little lonely. My mom and dad went off on a mission for our church, my brothers were still touring, Donny and Marie were doing their own thing – so I was kinda left behind, Billy no-mates, trying to figure out what to do. I lived on my own, though I wouldn’t recommend that, it was quite lonely.

Maybe my parents were worn down after nine kids but I had a lot more freedom than I’d ever give my kids. It was quite scary. I moved to California, where I was born – I’m the oddball in my family, they were all born in Utah – and ended up at a ridiculously young age brokering entertainment deals for other celebrities. I made my own money, and really – those were the best times of my life. You’re offered everything out there but you have to ask yourself, well, who am I? What do I really stand for? That’s why those teenage years are so critical.

Andy Williams has always been a hero to Jimmy.

If I met the teenage Jimmy now I’d think he was a nice kid but I’d see he didn’t know who he was. He was a bit all over the place with all these crazy projects. All kids are a bit like that but I was on turbo. I wanted to grow up so quickly. Groups like us got so much attention it was crazy, mayhem. With that came all sorts of security risks. We had security guards with us all the time. I used to have to wear a panic button round my neck when I was 14, due to the threats we got. [American self-styled left-wing revolutionaries] The Symbionese Liberation Army threatened to kidnap me. That’s kind of a mind trip. But I think the younger me would be happy with how things turned out. My mentor was Andy Williams and now I own his theatre – who would have thought that would happen?

I told Michael Jackson, I’m so glad that people saw the light, that you’re a good person.

I’ve made a lot of mistakes and had ups and downs but you learn most from your mistakes. In many ways, losing all our money was the best thing that ever happened to us [the band lost around $80m due to advisers’ mishandling]. What you have in the bank does not define you, and you can become an idiot if you have too much. I think now I have just enough. I have to work but I like to work.

If I could go back in time, I’d try harder to maintain my friendship with Michael Jackson. I used to work for him – I arranged his licensing for Smooth Criminal and the Bad album. He really blessed my life because at the time I really needed the work and he took my deal over others that would have given him more money. We had a pretty good friendship, and then he went through those struggles. I remember after he was acquitted from all that craziness [Jackson faced child molestation charges in 2005], I phoned him and said congratulations buddy, I’m so glad that people saw the light, that you’re a good person. I feel bad now that I didn’t really reconnect with him. I wasn’t the best friend, though he’d blessed my life so much financially. When I heard he’d died I felt so sad that was a friendship that was undone.

Jimmy with his friend Michael Jackson.

If I could go back to any time in my life it would be when I was able to put The Osmonds back together for one last round. It was our 50th anniversary and we did a big TV show and tour. It reconnected us because sometimes agents and managers get in the way. So I said, this is about me and my brothers. This one last time we’re going to put away our egos and celebrate this great past. My goodness, it took fire. I sold out three shows in Las Vegas in seven minutes.

I have this memory from the London O2 show. Alan was always the squadron leader, the man’s man, but he has MS now. He walked out onto the stage and we all looked at each other, and we started singing He Ain’t Heavy, He’s My Brother. Alan threw his cane into the sea of people in the arena and cried big tears, and we all just lost it. That was probably one of the happiest moments of my life. We began this music career as a family, and 50 years later we ended it as a family.

Jimmy Osmond will be touring Moon River & Me – A Tribute to Andy Williams from September 26